CN103031283B - Stevia rebaudiana enzyme VI and method for converting rebaudioside-A into rebaudioside-D - Google Patents
Stevia rebaudiana enzyme VI and method for converting rebaudioside-A into rebaudioside-D Download PDFInfo
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- CN103031283B CN103031283B CN201110299615.5A CN201110299615A CN103031283B CN 103031283 B CN103031283 B CN 103031283B CN 201110299615 A CN201110299615 A CN 201110299615A CN 103031283 B CN103031283 B CN 103031283B
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Abstract
The invention belongs to the field of food chemistry, and particularly relates to a method for converting RA (rebaudioside-A) which is taken as a raw material into RD (rebaudioside-D), and the key is stevia rebaudiana enzyme VI and a preparation method thereof. The converting method comprises the following steps: A, the RA of which the purity is higher than 90% is dissolved with water according to the weight measurement ratio of 1:6-1:10m/v; B, UDP-Glu (Uridine Diphosphate Glucose) is added according to the weight ratio that RA:UDP-Glu=15:5-15:9; C, the stevia rebaudiana enzyme VI is added according to the weight ratio that RA: stevia rebaudiana enzyme VI=(800-1200):1 (preferably 1000:1), and then reaction is carried out for 3-7h at the temperature of 40-60 DEG C and the pH of 6-8; and D, a reaction solution is filtered and dried to obtain RD-containing solid matter. The conversion rate of converting RA into RD is larger than or equal to 70%, and the RD content in the solid matter is 60%-70%, can achieve 80% after further separation and purification, and even can be larger than 90%.
Description
Technical field
The present invention relates to genus field of food chemical industry, be specifically related to take rebaudioside A as raw material, be converted into the method for Rebaudiodside A D by rebaudioside A, its key is catalyzer Stevia rebaudiana enzyme VI and preparation method thereof.
Background technology
Steviol glycoside is a general name to qualities of stevia extract, its sweet ingredient comprises stevioside (Stevioside), rebaudioside A, B, C, D, E (ebaudioside A/B/C/D/E), steviolbioside (Steviolbioside), Du Ke glycosides A (DulcosideA) etc.South America is originated in sweet Stevia source, has had the use history of centuries.Steviol glycoside sugariness is high, and the feature that heat is low has just in time met the needs of modern's life.The Ministry of Health of China on June 5th, 1985 (85) defends anti-word No. 37 literary composition, and approval steviol glycoside is classified as newly-increased foodstuff additive kind.The foodstuff additive joint specialist council of the World Health Organization (JointFAO/WHO Expert Committee on Food AdditVIes, JECFA) has also confirmed its security.
But traditional steviol glycoside is due to complicated component, and impurity is many, make it have rear bitter taste, this have impact on widely using of it and the market space.Research shows, in steviol glycoside, the mouthfeel of different glycoside component exists comparatively significantly difference, lists the relative sweetness of its different glucosides and relative saccharoid value in table 1.(Pure&Appl.Chem.，Vol.69，No.4，pp.675-683，1997.)
Table 1 steviol glycoside composition relative sweetness and relatively saccharoid
Rebaudioside A, Rebaudioside A (hereinafter referred to as RA) is a kind ofly further purified the sweeting agent obtained, the feature that existing sugariness is high, mouthfeel good, security is good on traditional steviol glycoside basis.RA molecular structural formula is shown in formula 1.But RA is compared with sucrose, still difference to some extent in mouthfeel, RA has faint rear bitter taste, plays sweet speed and returns sweet speed and sucrose also has difference.
Formula 1RA structural formula
Rebaudiodside A D, Rebaudioside D (hereinafter referred to as RD) and RA has identical mother nucleus structure (steviol), but RD is compared with RA multi-link glucose molecule on 19 side chains.RD molecular structural formula is shown in formula 2.Find in experiment, RD is in close proximity to sucrose in mouthfeel, does not have rear bitter taste.But the content of RD in steviol glycoside is far smaller than 1%, if produce RD by purifying steviol glycoside, its cost is very high, is difficult to produce in a large number and promote the use of.
Formula 2RD structural formula
Up to now, also not having with RA is raw material, is produced the report of RD by technological methods such as enzyme bio-transformation, ultrafiltration.
Summary of the invention
It is raw material with rebaudioside A that technical problem solved by the invention is to provide a kind of, is converted into the method for Rebaudiodside A D by rebaudioside A.
Particularly, method for transformation of the present invention is completed by following step:
A, by purity be > 90% rebaudioside A by 1: 6 ~ 1: 10m/v weightmeasurement ratio be dissolved in water;
B, add uridylic diphosphate glucose by following weight proportion, rebaudioside A: uridylic diphosphate glucose=15: 5 ~ 15: 9;
C, add Stevia rebaudiana enzyme VI by following weight proportion, rebaudioside A: Stevia rebaudiana enzyme VI=800-1200: 1 (preferably 1000: 1), then at 40 ~ 60 DEG C, pH 6 ~ 8 times reaction 3 ~ 7h;
D, filtering reacting liquid, be drying to obtain the solid substance containing Rebaudiodside A D.In solid substance, Rebaudiodside A D content is 60%-70%.
Concrete, step D filtering reacting liquid, is drying to obtain the solid substance containing Rebaudiodside A D: after can first being concentrated by reaction solution, then adopts common methods drying to obtain the solid substance containing Rebaudiodside A D.
In order to improve content and the purity of Rebaudiodside A D in solid substance, be separated Stevia rebaudiana enzyme VI wherein, 8-12kD ultrafiltration membrance filter is adopted when step D filtering reacting liquid, its objective is the Rebaudiodside A D in separating reaction liquid and Stevia rebaudiana enzyme VI, because Stevia rebaudiana enzyme VI molecular weight is 50 ~ 56kD, therefore Stevia rebaudiana enzyme VI can not pass through ultra-filtration membrane.Obtain ultrafiltration permeate after concentration through ultrafiltration membrance filter, conventional drying methods can be adopted can to obtain the higher solid substance of Rebaudiodside A D purity.
In order to separation, purifying obtain highly purified Rebaudiodside A D further, transmembrane pressure should control at 0.5 ~ 1.5MPa by ultrafiltration membrance filter.And during ultrafiltration concentration permeate, should control at 60-80 DEG C, avoid temperature too high and affect the yield of Rebaudiodside A D.In solid substance, Rebaudiodside A D content is 70%-80%.
In order to avoid wastage of material and be beneficial to environment protection, Stevia rebaudiana enzyme VI after ultra-filtration and separation can also be adopted the methods such as organic solution sex change precipitation, sieve chromatography be just separated, reclaim.
UDP-Glc, as one of raw material, because its physicochemical property and Rebaudiodside A D differ greatly, therefore can also adopt the mode such as column chromatography and crystallization to remove unreacted UDP-Glc and reacted UDP after reaction.After eliminating UDP-Glc, UDP, Stevia rebaudiana enzyme VI in solid substance, in solid substance, Rebaudiodside A D content is 80-90%, even can be greater than 90%.
The crucial part of method for transformation of the present invention is: utilize uridylic diphosphate glucose as saccharide donor, as catalyzer, rebaudioside A is converted into Rebaudiodside A D by Stevia rebaudiana enzyme VI.
As the key factor Stevia rebaudiana enzyme VI in method for transformation of the present invention, it is from sweet Stevia plant, extract the species specificity UDP-Glu glycosyltransferase obtained.Concrete, it utilizes following method to obtain:
(1) be 7.0-9.0 phosphate buffered saline buffer by sweet Stevia blade and pH value by 1: 2-1: 4m/v weightmeasurement ratio mix, carry out the broken 1-2h of cell walls after soaking 0.5-1h in 30-50 DEG C, obtain cytoplasm;
(2) centrifugation step (1) gained cytoplasm, gets supernatant liquor and crosses ultra-filtration membrane, and ultra-filtration membrane specification is 8-12kD, and transmembrane pressure controls at 1.0-1.5MPa, collects trapped fluid;
(3) use dextrane gel to press molecular weight to the segmentation of step (2) gained trapped fluid, its middle-molecular-weihydroxyethyl is Stevia rebaudiana enzyme VI at the enzyme of 50 ~ 56kD.
Preferably, the preparation method of Stevia rebaudiana enzyme VI is as follows:
(1) be 8.0 phosphate buffered saline buffers by sweet Stevia blade and pH value by 1: 3m/v weightmeasurement ratio mix, carry out the broken 1h of cell walls after soaking 0.5h in 40 DEG C, obtain cytoplasm;
(2) centrifugation step (1) gained cytoplasm, gets supernatant liquor and crosses ultra-filtration membrane, and ultra-filtration membrane specification is 10kD, and transmembrane pressure controls at 1.5MPa, collects trapped fluid;
(3) use dextrane gel to press molecular weight to the segmentation of step (2) gained trapped fluid, its middle-molecular-weihydroxyethyl is Stevia rebaudiana enzyme VI at the enzyme of 50 ~ 56kD.
Apply above-mentioned enzyme catalysis and separation method, take rebaudioside A as transformation efficiency >=70% that raw material obtains Rebaudiodside A D, in solid substance, Rebaudiodside A D content at least can reach 60%, can reach 80% after further separation and purification, even can > 90%, the mouthfeel free from extraneous odour of Rebaudiodside A D, closely similar with sucrose, can use as sweeting agent separately, produce RD cost in this approach low, easy amplification, is applicable to industrial production.
Embodiment
Illustrate below by way of specific description of embodiments of the present invention but do not limit the present invention.
In a specific embodiment, rebaudioside A is referred to as RA, and Rebaudiodside A D is referred to as RD, and uridylic diphosphate glucose is called for short UDP-Glu.
It is below the shaker test of carrying out for key parameter in method for transformation of the present invention.
The impact that test example 1 reaction substrate condition transforms RD
Embodiment 1 ~ 9 is investigate reaction substrate condition to the impact of RA bio-transformation, test with orthogonal test method, respectively 9 parts of 20g RA (95%) are carried out reaction substrate preparation by table 2 condition (1: 6 ~ 1: 10m/v, 10 ~ 40 DEG C, stirring velocity 60 ~ 120rpm, churning time 30 ~ 60min).After preparation, then make a gesture of measuring according to the weight of the ratio 15: 7,1000: 1m/m (RA dry powder: Stevia rebaudiana enzyme VI) of RA dry powder and UDP-Glu and add Stevia rebaudiana enzyme VI, what under pH value 7,50 DEG C of conditions, be incubated 5h carries out enzymatic bio-transformation.Reaction solution is crossed 10kD specification ultra-filtration membrane after bioconversion reaction, transmembrane pressure controls at 1.5MPa, and gets permeate respectively, adopts the HPLC detection method in GB GB8270-1999, detects the growing amount of RD, and calculates RD transformation efficiency, the results are shown in Table 2.
Table 2 reaction substrate condition test scheme and interpretation of result
The invention is not restricted to the specified conditions of the given conversion of RD in embodiment, purity and dissolving RA dry powder.
The impact that test example 2 biotransformation condition transforms RD
Embodiment 10 ~ 18 is investigate biotransformation condition to the impact of RD transformation efficiency, carries out orthogonal experiment with biotransformation condition factor.First, not by 9 parts of 20g RA (90%) by table 3 condition, by the ratio 1: 8, churning time 45min of RA dry powder and water, solvent temperature 25 DEG C, stirring velocity 90rpm carries out reaction substrate preparation.Then by RA: Stevia rebaudiana enzyme VI=1000: 1m/m adds Stevia rebaudiana enzyme VI, then according to table 2 condition (RA: UDP-Glu=15: 5 ~ 15: 9m/m, temperature 40 ~ 60 DEG C, acidity-basicity ph 6 ~ 8, reaction times 3 ~ 7h) carry out the orthogonal test of bio-transformation.Reaction solution is crossed 10kD specification ultra-filtration membrane after bioconversion reaction, transmembrane pressure controls at 1.5MPa, and gets permeate respectively, adopts the HPLC detection method in GB GB8270-1999, detects the growing amount of RD, and calculates RD transformation efficiency, the results are shown in Table 3.
Table 3 biotransformation condition is on the impact of RD transformation efficiency
The invention is not restricted to the specified conditions of the given conversion of RD in embodiment, purity and ferment treatment RA.
Test example 3 investigates the impact that ultrafiltration transmembrane pressure reclaims Stevia rebaudiana enzyme VI
For investigating ultrafiltration transmembrane pressure to the recovery of Stevia rebaudiana enzyme VI, point three gradients select suitable ultrafiltration transmembrane pressure.By the ratio 1: 10 of 500g95%RA dry powder and water, 40 DEG C of churning time 1h dissolve, the ratio 15: 7 of RA dry powder and UDP-Glu, make a gesture of measuring according to the weight of 1000: 1m/m (RA dry powder: Stevia rebaudiana enzyme VI) and add Stevia rebaudiana enzyme VI, temperature of reaction 50 DEG C, pH value 7, the condition of reaction times 7h carries out ferment treatment.Ferment treatment liquid is crossed 10kD specification ultra-filtration membrane, transmembrane pressure controls respectively at 0.5MPa, 1.0MPa, 1.5MPa, and gets trapped fluid respectively and permeate detects its solid content, investigates the impact that ultrafiltration transmembrane pressure reclaims Stevia rebaudiana enzyme VI, the results are shown in Table 4.
The impact that table 4 ultrafiltration transmembrane pressure reclaims Stevia rebaudiana enzyme VI
When ultrafiltration transmembrane pressure is at 0.5 ~ 15MPa, enzyme changes stevioside through 10kD specification ultra-filtration membrane, can play the effect that Stevia rebaudiana enzyme VI and RD is separated, and can reclaim Stevia rebaudiana enzyme VI simultaneously.
The invention is not restricted to the specified conditions of the given conversion of RD in embodiment, alcoholic degree and ultrafiltration transmembrane pressure.
Embodiment 4 investigates filtration, method of enrichment to the impact of solid substance RD content
After obtaining reaction solution according to the method for transformation of embodiment 1-18, according to filter paper filtering, dry, obtain solid substance A; According to the ultrafiltration of 10kD specification ultra-filtration membrane, dry ultrafiltration permeate obtains solid substance B; Obtain solid substance C according to by drying after ultrafiltrated recrystallize, adopt the HPLC detection method in GB GB8270-1999 to detect RD, the results are shown in Table 5.
Table 5
As seen from Table 5, in solid substance A, Rebaudiodside A D content at least can reach 60%, and the red RD of solid substance C after refining further can reach 80%, even can be greater than 90%.
To sum up, applying above-mentioned enzyme catalysis and separation method, is transformation efficiency >=70% that raw material obtains Rebaudiodside A D with rebaudioside A, and in solid substance, Rebaudiodside A D content at least can reach 60%, can 80% be reached after further separation and purification, even can be greater than 90%, the mouthfeel free from extraneous odour of Rebaudiodside A D, closely similar with sucrose, can use as sweeting agent separately, produce RD cost in this approach low, easily amplify, be applicable to industrial production.
Claims (9)
1. rebaudioside A is converted into the method for Rebaudiodside A D, it is characterized in that: its step is as follows:
A, be that the rebaudioside A of >90% is dissolved in water by the weightmeasurement ratio of 1:6 ~ 1:10 m/v by purity;
B, add uridylic diphosphate glucose by following weight proportion, rebaudioside A: uridylic diphosphate glucose=15:5 ~ 15:9;
C, add Stevia rebaudiana enzyme VI by following weight proportion: rebaudioside A 800-1200 part, Stevia rebaudiana enzyme VI 1 part, then at 40 ~ 60 DEG C, pH 6 ~ 8 times reaction 3 ~ 7h;
D, filtering reacting liquid, be drying to obtain the solid substance containing Rebaudiodside A D;
Wherein, Stevia rebaudiana enzyme VI extracts to obtain from the leaf of sweet Stevia, and preparation method is as follows:
(1) be that 7.0-9.0 phosphate buffered saline buffer mixes by the weightmeasurement ratio of 1:2-1:4 m/v by sweet Stevia blade and pH value, carry out the broken 1-2 h of cell walls after soaking 0.5-1 h in 30-50 DEG C, obtain cytoplasm;
(2) centrifugation step (1) gained cytoplasm, gets supernatant liquor and crosses ultra-filtration membrane, and ultra-filtration membrane specification is 8-12 kD, and transmembrane pressure controls at 1.0-1.5MPa, collects trapped fluid;
(3) use dextrane gel to press molecular weight to the segmentation of step (2) gained trapped fluid, its middle-molecular-weihydroxyethyl is Stevia rebaudiana enzyme VI at the enzyme of 50 ~ 56kD.
2. rebaudioside A according to claim 1 is converted into the method for Rebaudiodside A D, it is characterized in that: when in steps A, rebaudioside A is dissolved in water, and water temperature controls at 30 ~ 40 DEG C.
3. rebaudioside A according to claim 1 is converted into the method for Rebaudiodside A D, it is characterized in that: after in steps A, rebaudioside A is dissolved in water, and stirs 30 ~ 60 min with the speed of 60 ~ 120rpm.
4. rebaudioside A according to claim 1 is converted into the method for Rebaudiodside A D, it is characterized in that: adopt 8-12kD ultrafiltration membrance filter during step D filtering reacting liquid.
5. rebaudioside A according to claim 4 is converted into the method for Rebaudiodside A D, it is characterized in that: after step D filtering reacting liquid, concentration.
6. rebaudioside A according to claim 5 is converted into the method for Rebaudiodside A D, it is characterized in that: described concentrated condition is at 60-80 DEG C of concentration of reaction solution.
7. rebaudioside A according to claim 1 is converted into the method for Rebaudiodside A D, it is characterized in that: step C adds Stevia rebaudiana enzyme VI by following weight proportion: rebaudioside A 1000 parts, Stevia rebaudiana enzyme VI 1 part.
8. rebaudioside A according to claim 1 is converted into the method for Rebaudiodside A D, it is characterized in that: when step D filters, transmembrane pressure controls at 0.5 ~ 1.5MPa.
9. rebaudioside A according to claim 1 is converted into the method for Rebaudiodside A D, it is characterized in that: Stevia rebaudiana enzyme VI extracts to obtain from the leaf of sweet Stevia, and preparation method is as follows:
(1) be that 8.0 phosphate buffered saline buffers mix by the weightmeasurement ratio of 1:3 m/v by sweet Stevia blade and pH value, carry out the broken 1h of cell walls after soaking 0.5h in 40 DEG C, obtain cytoplasm;
(2) centrifugation step (1) gained cytoplasm, gets supernatant liquor and crosses ultra-filtration membrane, and ultra-filtration membrane specification is 10kD, and transmembrane pressure controls at 1.5MPa, collects trapped fluid;
(3) use dextrane gel to press molecular weight to the segmentation of step (2) gained trapped fluid, its middle-molecular-weihydroxyethyl is Stevia rebaudiana enzyme VI at the enzyme of 50 ~ 56kD.
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| CN103397064B (en) * | 2013-08-14 | 2015-04-15 | 苏州汉酶生物技术有限公司 | Method for preparing rebaudioside M through enzyme method |
| CA2987585C (en) * | 2015-05-29 | 2023-08-29 | Cargill, Incorporated | Fermentation methods for producing steviol glycosides using high ph and compositions obtained therefrom |
| CN108884484A (en) * | 2015-11-30 | 2018-11-23 | 谱赛科有限责任公司 | The method for being used to prepare high-purity steviol glycoside |
| US11352653B2 (en) | 2016-10-21 | 2022-06-07 | Pepsico, Inc. | Enzymatic method for preparing rebaudioside N |
| AU2016427120B2 (en) | 2016-10-21 | 2022-08-18 | Pepsico, Inc. | Method for preparing rebaudioside C using enzymatic method |
| CA3041147A1 (en) | 2016-10-21 | 2018-04-26 | Pepsico, Inc. | Method for preparing rebaudioside j using enzymatic method |
| US11274328B2 (en) * | 2018-09-29 | 2022-03-15 | Sichuan Ingia Biosynthetic Co., Ltd. | Methods for producing rebaudioside D and rebaudioside M and compositions thereof |
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| CN101156883A (en) * | 2007-10-24 | 2008-04-09 | 石任兵 | Stevia rebaudian valid target as well as its activity and application |
| ES2901901T3 (en) * | 2007-12-03 | 2022-03-24 | Dsm Ip Assets Bv | New nutraceutical compositions containing steviol and their use |
| CN101805768B (en) * | 2010-03-01 | 2012-03-21 | 江苏健佳药业有限公司 | Biological enzymolysis and purification method of high-quality stevioside |
| CN101775425A (en) * | 2010-03-24 | 2010-07-14 | 江南大学 | Method for catalyzing and synthetizing modified stevioside by using microwave auxiliary cyclodextrin glucosyltransferase |
| BR112012030836B8 (en) * | 2010-06-02 | 2024-02-06 | Evolva Nutrition Inc | Recombinant host comprising recombinant genes for producing steviol or steviol glycoside, method for producing steviol, steviol glycoside or steviol glycoside composition and method for synthesizing steviol or steviol glycoside |
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